Copper-catalyzed cross-coupling of α-seleno-acylzirconocene chloride with haloalkynes: Synthesis of α-seleno-substituted vinyl alkynyl ketones

The copper-catalyzed cross-coupling reaction of α-selenoacylzirconocene chloride 3 with haloalkynes in the presence of carbon monoxide gives α-seleno-substituted vinyl alkynyl ketones 5 in moderate yields. The reaction conditions are neutral and mild enough (room temperature, 1 atm carbon monoxide) that other functional groups in either coupling partner can be brought unaltered into the coupled product. The E geometry in the α-alkylseleno vinylzirconocene reagent is maintained during the coupling reaction. © 2000 John Wiley & Sons, Inc. Heteroatom Chem 11:91–93, 2000